Structure of 111409-79-1
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CAS No. : | 111409-79-1 |
Formula : | C11H21BrSi |
M.W : | 261.27 |
SMILES Code : | CC([Si](C(C)C)(C#CBr)C(C)C)C |
MDL No. : | MFCD11036302 |
InChI Key : | HNNUBQWDWJNURV-UHFFFAOYSA-N |
Pubchem ID : | 11196280 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The reaction formula of this embodiment is as follows: 1) Under air, IMesCuCl (3 molpercent),Potassium carbonate (1.1 eq), bis(pinacolato)diboron (1 eq) was added to a pressure-resistant sealed reaction tube containing a magnetic particle. After filling with acetylene,3 mL of tetrahydrofuran was added to the reaction tube.Stir at room temperature for 20 minutes,Then add triisopropylsilyl bromoacetylene (0.25 mmol) to the reaction solution,The reaction was stirred in a 30 ° C oil bath for 12 hours.(2) The material obtained in the step (1) is cooled to room temperature, and thoroughly mixed with ethyl acetate. After filtering off the solid residue with a short silica gel column, the organic phase was retained.(3) spinning the solvent in the organic phase obtained in the step (2) to obtain a crude product.The crude product was then purified on a silica gel column. The eluent is a mixed solution of petroleum ether and ethyl acetate.And the ratio of petroleum ether to ethyl acetate is 50:1. The isolated yield was 78percent.The product was 99percent pure. The prepared product was subjected to structural characterization, and the results are shown in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With cesium acetate; In 1,2-dichloro-ethane; at 100℃; for 12h;Inert atmosphere; Schlenk technique; | Under a nitrogen atmosphere,An arylamide compound 1d (17.1 mg, 0.10 mmol), alkynyl bromide or alkyne 2 (30 muL, 0.15 mmol) was added to a 15 mL reaction tube.Dichloro(pentamethylcyclopentadienyl) ruthenium dimer (2.3 mg, 0.0025 mmol),Or dichloro(p-methylisopropyl) ruthenium dimer (1.5mg, 0.0025mmol),Silver bis(trifluoromethanesulfonyl)imide (6.0 mg, 0.015 mmol) or silver hexafluoroantimonate (5.3 mg, 0.015 mmol), sodium acetate (30 mg, 0.36 mmol), silver acetate (20 mg, 0.12 mmol) (when the reaction uses an alkyne bromide, no additional oxidant is needed; when the reaction uses a terminal alkyne directly, 2 equivalents of silver acetate is required),1,2-Dichloroethane (DCE, 1 mL), mixed, and reacted at 100 ° C for 12 hours.After completion of the reaction, the mixture was cooled to room temperature, filtered under vacuum and concentrated to give a crude material. The crude product was chromatographed on the prepared silica gel plate, and the selected developing solvent was a petroleum ether to ethyl acetate volume ratio of 20:1.The product 3-((triisopropylsilyl)acetylene)-2-naphthalenecarboxamide (3d) was obtained:Yellow solid, yield 92percent (30.3 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) acetate; sodium acetate; silver(I) triflimide; In 1,2-dichloro-ethane; at 120℃; under 760.051 Torr; for 12h;Schlenk technique; Inert atmosphere; | 1 g (42.4 mg, 0.20 mmol) of a phenylacetamide compound and a trivalent ruthenium catalyst [Cp*IrCl2] 2 (1.60 mg, 0.002 mmol) were sequentially added to a 15 mL Schlenk reaction tube under an atmosphere of atmospheric pressure.Bis-trifluoromethanesulfonimide silver salt (3.9 mg, 0.01 mmol), sodium acetate (2.5 mg, 0.03 mmol), silver acetate (10.0 mg, 0.06 mmol),Finally, a solution of the alkynyl compound 2a (20 μL, 0.30 mmol) in 1,2-dichloroethane (DCE, 1 mL) was charged into the reactor with a syringe and reacted at a temperature of 120 C for 12 h.After completion of the reaction, the mixture was cooled to room temperature, suction filtered over Celite, and evaporated.The crude product was chromatographed on the prepared silica gel plate, and the selected developing solvent or eluent was petroleum ether and ethyl acetate in a volume ratio of 10:1.The product 2-(5-bromo-2-((triisopropyl)ethynyl)phenyl)acetamide (3 g) was obtained, 51.1 mg, yield 65%, purity 95%. |